Mastering Corporate Retreats for Startups: Part II - Engaging Activities For All

March 5, 2024
Milana Martinovic

Milana has been involved in hospitality and events her entire career. Her journey in operations, support and distributed work started with Airbnb and continues among other startups in the ever evolving tech space. The two worlds connected 6 years ago when Milana got involved with building one of the frontrunners in the company retreat market in the evolving space of remote work. OnsiteHub was created as a culmination of 20 years experience in hospitality, tourism and startups to help distributed teams get together and enhance culture and connection.

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Once you have received approval for your team's retreat from your company’s C-suite and investors (using the tactics we covered in Part I: Advocating & Planning), it’s time to start planning the event. And one of the key ingredients in any successful company retreat is the balance between work and play. When I was tasked to plan my company’s first ever retreat, finding ways to make it engaging and enjoyable was one of my primary goals.  

In this article, I’ll be sharing some great activities to learn more about your colleagues, develop relationships with other departments, and enjoy the rare time that you have together in-person, especially if you are a solely remote company. 

Pre-Planning and Knowing Your Audience

First of all, it’s important to think through the variety of employees who will be attending the retreat. You might have the CEO and an intern meeting each other in person for the first time. You could have team members from a western European country, as well as an eastern Asian country, who have different cultures and ways of interacting with one another. You may have sales representatives who have met previously at conferences or perhaps you’ll have tech developers who are more comfortable behind a screen. It’s essential to curate a retreat that considers the comfortability of each employee and to plan activities that can appeal to a range of personalities.  

It is important to both dedicate time to fun activities and to enjoy the locale - you are on a retreat after all, hopefully somewhere sunny! But it is also important to dedicate a portion of the day to work. Find the right balance, and everyone from manager to associate will thank you.

Four Work Activities That Actually Deliver!

Here’s a look at how I approached planning our company retreat with the goal of fostering engagement through activities.

On the first day, our focus was on getting to know members of other teams. Working remotely has its incredible benefits, but it is easy to get siloed. When meeting each other in person, maybe for the first time, don’t miss the opportunity to brainstorm with colleagues whom you don’t normally interact with. 

On the second day, we hosted an all team forum, where all colleagues were encouraged to ask questions of the founders and C-suite personnel. Everyone was excited to learn how the company started, and hear each manager’s vision for the future of the company. A typical speech from the CEO is great, but this was personal and engaging,and made us all feel like  part of the team. 

Here are some organized activities to try with your team and how they benefited our group::

  1. Round Tables: Randomly pair different members of different teams together. I remember meeting a QA developer from the tech department, and finally understanding what his role was (“QA” stands for “quality assurance”). For the first time, I felt fully connected to the company and product. 
  2. Colleague “Speed Dating: This was a fun one! We did this on the first day to warm people up to each other. Everyone had 2 minutes to strike up a short discussion with someone else. We provided a few fun icebreaker questions to encourage conversation before the timer rang and it was time to meet with someone else. 
  3. Open Forum with Founders or Managers: As mentioned above, this was an interactive way in which everyone could ask all their burning questions of the founders. You can encourage employees to send in their questions anonymously prior to the retreat so everyone feels comfortable sharing,however, usually after the first few questions are asked, people will jump right in.. 
  4. Employee Feedback: We asked everyone to turn in three to four ideas anonymously. The company built on those ideas and created what is now their value and vision blueprint. Additionally, it was interesting to hear what everyone expressed and for everyone to feel like they were helping create the building blocks of the team. 

Five Fun Activities for Your Team Retreat 

After a morning of hard work, it is important to dedicate your afternoons to some fun. After all, this is a time to get to know each other, and what better way to do that than to plan some interesting activities for everyone to enjoy? For many, this could be the only time of the year where they see their colleagues in person. 

Below are a few ideas that could be customized to suit your team’s personalities and dynamic. And it’s  important to always have alternatives, just in case there are those that don’t wish to participate in a certain activity. 

  1. Hiking: I find walking with someone can be the best way to have a conversation. Ask a local guide to take your group on an easy hike through some beautiful landscapes. Ensure that it is doable for all levels, and make sure everyone brings water. Let the atmosphere inspire you and watch the innovation flow! 
  2. Obstacle Course: Where we were in Mallorca, there was a great location that had both an obstacle course, paintball, and other activities in one place. The obstacle course was hilarious - it was a great way to get everyone out of their comfort zones. And paintball was a great team building exercise! However, ensure that there is also an area to chill and have a drink, for of course there will be those who don’t wish to participate. No one should ever feel forced to join in - that is essential in any large group. 
  3. Wine or Food Tastings: This activity is especially great for a small group, or perhaps for a management retreat. We had a guide explaining all of the wines we were tasting and gave us a topic to discuss. However, be sure ahead of time that everyone in your group drinks alcohol - don’t assume anything. Another idea could be a chocolate or other local food tasting. 
  4. Cooking Class: Cooking together encourages teamwork. You are building something together with a delicious result! Plus, if you normally work behind a computer, this is something more tangible that you can do. It makes for a nice change and also requires more discussion and conversation which you can later translate to a remote work environment. 
  5. Boat or Sightseeing Trip: Many people may not travel frequently and might want to enjoy exploring the locale.. We took an all day boat ride, stopping for lunch and some beach time.. It was a relaxing day that took us away from our computers and into the sunshine. Most of my colleagues said that this was their favorite day of the whole trip because they could both enjoy the water and experience it with new connections. 

Final Thoughts

There are two more important things to keep in mind when planning activities for your trip: 

  1. Eat Together! The most wonderful times were when we ate dinner together. Ask your hotel or guide to provide restaurant suggestions, make sure that you have a variety of food selections, and enjoy. Nothing bonds people together more than food, and I will never forget the paella I had in Spain while sitting with my marketing team. 
  2. Free Time! There will be many people who will need to recharge their social battery (me being one of them!) and will need to take a break during the day to do so. There will be others who will want to take some time to buy a souvenir for their kids and still others who have to take meetings with outside clients. Scheduling in free time helps to avoid burnout, so that everyone walks away with only the best memories. 

As remote and flexible working environments grow and become the norm, it is essential to create an experience for your team that promotes teamwork, innovation, and fun! Always consider the different cultures and size of the company, and think about the location as well. But once that retreat is over, you will need to consider how to build on the connections you have cultivated. See how in the next article of this series!

If you are an in-house corporate event manager that needs a little assistance, consider working with a dedicated company retreat company like OnsiteHub, whose mission it is to create meaningful retreat experiences across the best locations in Europe that foster unity, enhance communication, and spark innovation.

Having help from an outside company who specializes in planning team retreats can allow you to focus solely on creating an impactful event strategy that will have an undeniably positive impact on your company. 

Good luck!


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